DE19531895A1 - Verfahren zur Herstellung von 4-Cyano-2,5-difluoranilin - Google Patents
Verfahren zur Herstellung von 4-Cyano-2,5-difluoranilinInfo
- Publication number
- DE19531895A1 DE19531895A1 DE19531895A DE19531895A DE19531895A1 DE 19531895 A1 DE19531895 A1 DE 19531895A1 DE 19531895 A DE19531895 A DE 19531895A DE 19531895 A DE19531895 A DE 19531895A DE 19531895 A1 DE19531895 A1 DE 19531895A1
- Authority
- DE
- Germany
- Prior art keywords
- cyano
- preparation
- difluoroaniline
- diluent
- ammonia
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- LAPGMTOHOQPDGI-UHFFFAOYSA-N 4-amino-2,5-difluorobenzonitrile Chemical compound NC1=CC(F)=C(C#N)C=C1F LAPGMTOHOQPDGI-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000003085 diluting agent Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- DLKNOGQOOZFICZ-UHFFFAOYSA-N 2,4,5-trifluorobenzonitrile Chemical compound FC1=CC(F)=C(C#N)C=C1F DLKNOGQOOZFICZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000004009 herbicide Substances 0.000 abstract description 3
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 3
- 239000013067 intermediate product Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- JYUXDXWXTPSAEL-UHFFFAOYSA-N 1,4-dioxane;oxolane Chemical compound C1CCOC1.C1COCCO1 JYUXDXWXTPSAEL-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- RPZXUSJCSDQNTE-UHFFFAOYSA-N 2,4-dichloro-5-fluorobenzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=C(Cl)C=C1Cl RPZXUSJCSDQNTE-UHFFFAOYSA-N 0.000 description 1
- LJFDXXUKKMEQKE-UHFFFAOYSA-N 2,4-difluorobenzonitrile Chemical compound FC1=CC=C(C#N)C(F)=C1 LJFDXXUKKMEQKE-UHFFFAOYSA-N 0.000 description 1
- YNOOQIUSYGWMSS-UHFFFAOYSA-N 2,5-difluoroaniline Chemical compound NC1=CC(F)=CC=C1F YNOOQIUSYGWMSS-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- XOYHFIQPPOJMFK-UHFFFAOYSA-N 4-bromo-2,5-difluoroaniline Chemical compound NC1=CC(F)=C(Br)C=C1F XOYHFIQPPOJMFK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- -1 methyl t-butyl Chemical compound 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19531895A DE19531895A1 (de) | 1995-08-30 | 1995-08-30 | Verfahren zur Herstellung von 4-Cyano-2,5-difluoranilin |
| ES96928476T ES2146015T3 (es) | 1995-08-30 | 1996-08-19 | Procedimiento para la obtencion de 4-ciano-2,5-difluoranilina. |
| BR9610020A BR9610020A (pt) | 1995-08-30 | 1996-08-19 | Processo para a preparação de 4-ciano-2,5-difluoroanilina |
| DE59605320T DE59605320D1 (de) | 1995-08-30 | 1996-08-19 | Verfahren zur herstellung von 4-cyano-2,5-difluoranilin |
| CA002230509A CA2230509A1 (en) | 1995-08-30 | 1996-08-19 | 4-cyano-2,5-difluoraniline preparation process |
| HK99101113.2A HK1016154B (en) | 1995-08-30 | 1996-08-19 | Process for preparing 4-cyano-2,5-difluoroaniline |
| AU68225/96A AU6822596A (en) | 1995-08-30 | 1996-08-19 | 4-cyano-2,5-difluoraniline preparation process |
| CN96196648A CN1068869C (zh) | 1995-08-30 | 1996-08-19 | 制备4－氰基－2,5－二氟苯胺的方法 |
| US09/011,943 US6075160A (en) | 1995-08-30 | 1996-08-19 | 4-cyano-2,5-difluoroaniline preparation process |
| DK96928476T DK0854859T3 (da) | 1995-08-30 | 1996-08-19 | Fremgangsmåde til fremstilling af 4-cyano-2,5-difluoranilin |
| PCT/EP1996/003642 WO1997008136A1 (de) | 1995-08-30 | 1996-08-19 | Verfahren zur herstellung von 4-cyano-2,5-difluoranilin |
| EP96928476A EP0854859B1 (de) | 1995-08-30 | 1996-08-19 | Verfahren zur herstellung von 4-cyano-2,5-difluoranilin |
| KR1019980701365A KR19990044132A (ko) | 1995-08-30 | 1996-08-19 | 4-시아노-2,5-디플루오르아닐린의 제조 방법 |
| JP9509799A JPH11511443A (ja) | 1995-08-30 | 1996-08-19 | ４−シアノ−２，５−ジフルオロアニリンの製造方法 |
| MXPA/A/1998/001604A MXPA98001604A (en) | 1995-08-30 | 1998-02-27 | Farmaceuti compounds |
| MXPA/A/1998/001595A MXPA98001595A (es) | 1995-08-30 | 1998-02-27 | Procedimiento para la obtencion de 4-ciano-2,5-difluoranilina |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19531895A DE19531895A1 (de) | 1995-08-30 | 1995-08-30 | Verfahren zur Herstellung von 4-Cyano-2,5-difluoranilin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19531895A1 true DE19531895A1 (de) | 1997-03-06 |
Family
ID=7770760
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19531895A Withdrawn DE19531895A1 (de) | 1995-08-30 | 1995-08-30 | Verfahren zur Herstellung von 4-Cyano-2,5-difluoranilin |
| DE59605320T Expired - Fee Related DE59605320D1 (de) | 1995-08-30 | 1996-08-19 | Verfahren zur herstellung von 4-cyano-2,5-difluoranilin |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59605320T Expired - Fee Related DE59605320D1 (de) | 1995-08-30 | 1996-08-19 | Verfahren zur herstellung von 4-cyano-2,5-difluoranilin |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6075160A (pt) |
| EP (1) | EP0854859B1 (pt) |
| JP (1) | JPH11511443A (pt) |
| KR (1) | KR19990044132A (pt) |
| CN (1) | CN1068869C (pt) |
| AU (1) | AU6822596A (pt) |
| BR (1) | BR9610020A (pt) |
| CA (1) | CA2230509A1 (pt) |
| DE (2) | DE19531895A1 (pt) |
| DK (1) | DK0854859T3 (pt) |
| ES (1) | ES2146015T3 (pt) |
| WO (1) | WO1997008136A1 (pt) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109678741B (zh) * | 2019-01-29 | 2021-11-30 | 金凯(辽宁)生命科技股份有限公司 | 4-氨基-3-氟苯甲酸的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4504660A (en) * | 1982-07-06 | 1985-03-12 | American Home Products Corporation | Process for the production of 2,6-diaminobenzonitrile derivatives |
| ES2021267B3 (es) * | 1985-10-17 | 1991-11-01 | American Cyanamid Co | Metodo para promover el crecimiento, mejorar la eficacia alimenticia y para acelerar el engorde en animales de sangre caliente. |
| US4863959A (en) * | 1985-10-17 | 1989-09-05 | American Cyanamid Company | Anthranilonitrile derivatives as useful agents for promoting growth, improving feed efficiency, and for increasing the lean meat to fat ratio of warm-blooded animals |
| GB8919679D0 (en) * | 1989-08-31 | 1989-10-11 | Ici Plc | Fluorobenzene derivatives |
| JPH0565250A (ja) * | 1991-01-28 | 1993-03-19 | Ishihara Sangyo Kaisha Ltd | ３，５−ジフルオロアニリンの製造方法 |
-
1995
- 1995-08-30 DE DE19531895A patent/DE19531895A1/de not_active Withdrawn
-
1996
- 1996-08-19 DK DK96928476T patent/DK0854859T3/da active
- 1996-08-19 US US09/011,943 patent/US6075160A/en not_active Expired - Fee Related
- 1996-08-19 CA CA002230509A patent/CA2230509A1/en not_active Abandoned
- 1996-08-19 CN CN96196648A patent/CN1068869C/zh not_active Expired - Fee Related
- 1996-08-19 ES ES96928476T patent/ES2146015T3/es not_active Expired - Lifetime
- 1996-08-19 JP JP9509799A patent/JPH11511443A/ja active Pending
- 1996-08-19 AU AU68225/96A patent/AU6822596A/en not_active Abandoned
- 1996-08-19 WO PCT/EP1996/003642 patent/WO1997008136A1/de not_active Ceased
- 1996-08-19 KR KR1019980701365A patent/KR19990044132A/ko not_active Abandoned
- 1996-08-19 EP EP96928476A patent/EP0854859B1/de not_active Expired - Lifetime
- 1996-08-19 DE DE59605320T patent/DE59605320D1/de not_active Expired - Fee Related
- 1996-08-19 BR BR9610020A patent/BR9610020A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0854859A1 (de) | 1998-07-29 |
| BR9610020A (pt) | 1999-07-06 |
| HK1016154A1 (en) | 1999-10-29 |
| DE59605320D1 (de) | 2000-06-29 |
| ES2146015T3 (es) | 2000-07-16 |
| CN1194634A (zh) | 1998-09-30 |
| US6075160A (en) | 2000-06-13 |
| JPH11511443A (ja) | 1999-10-05 |
| CA2230509A1 (en) | 1997-03-06 |
| MX9801604A (es) | 1998-05-31 |
| EP0854859B1 (de) | 2000-05-24 |
| DK0854859T3 (da) | 2000-09-25 |
| WO1997008136A1 (de) | 1997-03-06 |
| CN1068869C (zh) | 2001-07-25 |
| KR19990044132A (ko) | 1999-06-25 |
| MX9801595A (es) | 1998-05-31 |
| AU6822596A (en) | 1997-03-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |